十二烷基-2,3,4,6-四-氧-乙酰基-β-D-吡喃氨基葡萄糖苷 | 211567-22-5

• 物质功能分类: 生物化工 - 糖类化合物 - 单糖
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 十二烷基-2,3,4,6-四-氧-乙酰基-β-D-吡喃氨基葡萄糖苷
• 中文别名: 十二烷基-2,3,4,6-四-氧-乙酰基-Β-D-吡喃氨基葡萄糖苷
• 英文名称: dodecyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside
• 英文别名: Dodecyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta-D-glucopyranoside；[(2R,3S,4R,5R,6R)-5-acetamido-3,4-diacetyloxy-6-dodecoxyoxan-2-yl]methyl acetate
• CAS: 211567-22-5
• 化学式: C₂₆H₄₅NO₉
• 分子量: 515.645
• InChiKey: PIEYYMFAQMSYFF-ZFXZZAOISA-N

物化性质

• 熔点：
  103-105℃ (ethyl ether )
• 沸点：
  616.7±55.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  36
• 可旋转键数：
  20
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  127
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  十二烷基-2,3,4,6-四-氧-乙酰基-β-D-吡喃氨基葡萄糖苷 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 30.0h， 生成 十二烷基-2-乙酰氨基-2-脱氧-β-D-吡喃葡糖苷
  参考文献：
  名称：

  糖的烷基化剂。衍生自2-氨基-2-脱氧-d-阿洛糖的环磷酰胺

  摘要：

  摘要通过用相应的2-氨基-2-脱氧-d-阿洛糖衍生物处理相应的2-氨基-2-脱氧-d-阿洛糖衍生物，以良好的收率合成了衍生自烷基2-氨基-4,6-O-亚苄基-2-脱氧-β-d-阿洛吡喃糖苷的环磷酰胺。双（2-氯乙基）磷酰胺二氯化物。成环反应以非常高的非对映选择性发生。随后的氢解得到了衍生自烷基2-氨基-2-脱氧-β-d-allopyranosides的优异的环磷酰胺收率，其亲水性大于前体。起始原料可容易地从2-乙酰氨基-2-脱氧-d-葡萄糖获得。

  DOI：

  10.1016/s0008-6215(98)00056-1
• 作为产物：
  描述：

  十二烷醇 、 (3aR)-2-甲基-5alpha-(乙酰氧基甲基)-6beta,7alpha-二乙酰氧基-3Aalpha,6,7,7Aalpha-四氢-5H-吡喃并[3,2-d]恶唑 在 对甲苯磺酸 作用下， 以 1,2-二氯乙烷 为溶剂， 以82%的产率得到十二烷基-2,3,4,6-四-氧-乙酰基-β-D-吡喃氨基葡萄糖苷
  参考文献：
  名称：

  Synthesis and protective anti-infective action of anomeric lipophilic glycosides of N-acetylmuramyl-L-alanyl-D-isoglutamine

  摘要：

  Anomeric pairs of alpha- and beta-dodecyl, alpha- and beta-(1-pentylhexyl), and alpha- and beta-cyclododecyl glycosides of N-acetylmuramyl-L-alanyl-D-isoglutamine (MDP) were synthesized. The starting beta-D-glucosaminides were obtained by the oxazoline method, and the corresponding alpha-isomers, by the mercuric iodide-catalyzed glycosylation of alcohols with alpha-glucosaminyl chloride peracetate in nitromethane at -90 degrees C. No reliable differences between the stimulation of mouse resistance to the infection with Staphylococcus aureus (doses of 2, 20, and 200 mu g/mouse) and Escherichia coli (doses of 0.05, 1, and 20 mu g/mouse) with the MDP alpha- and beta-glycosides were found.

  DOI：

  10.1134/s1068162006040091

文献信息

• H2SO4-Silica Promoted Direct Formation of β-Glycosides of N-Acetyl Glycosylamines under Microwave Conditions
  作者：Balaram Mukhopadhyay、Santanu Mandal、Nayan Sharma

  DOI：10.1055/s-0029-1218304

  日期：2009.12

  N-Acetyl glycosamines are important building blocks for the synthesis of biologically active oligosaccharides. This communication describes a simple direct protocol for the synthesis of β-glycosides of N-acetyl glycosylamines from easily accessible per-O-acetyl derivatives of of N-acetyl glycosylamines using H2SO4-silica as promoter under microwave conditions. The protocol is suitable for alcohol or sugar acceptors.

  N-乙酰氨基糖是生物活性低聚糖合成的重要构建单元。本通信介绍了一种简单直接的方法，利用微波条件下以硫酸-硅胶为促进剂，从易得的N-乙酰氨基糖的全O-乙酰衍生物合成N-乙酰氨基糖的β-糖苷。该方法适用于醇或糖类受体。
• Effect of Aglycon Structure on Saccharide Elongation by Cells
  作者：Tamami Kimura、Maria Carmelita Z. Kasuya、Kenichi Hatanaka、Koji Matsuoka

  DOI：10.1002/cbdv.201400278

  日期：2015.2

  Alkyl N‐acetyl‐β‐D‐glucosaminide (GlcNAc primers) with different aglycon moieties were synthesized and used to determine the effect of the aglycon structure on cellular saccharide elongation. Dodecyl N‐acetyl‐β‐D‐glucosaminide (GlcNAc‐C12), tridecan‐7‐yl N‐acetyl‐β‐D‐glucosaminide (GlcNAc‐2C6), and pentacosan‐13‐yl N‐acetyl‐β‐D‐glucosaminide (GlcNAc‐2C12) primers were synthesized by glycosylation of

  合成了具有不同苷元部分的烷基 N-乙酰基-β-D-氨基葡萄糖（GlcNAc 引物），并用于确定苷元结构对细胞糖延伸的影响。十二烷基 N-乙酰基-β-D-氨基葡萄糖 (GlcNAc-C12)、十三烷基-7-基 N-乙酰基-β-D-氨基葡萄糖 (GlcNAc-2C6) 和五十二烷-13-基 N-乙酰基-β-D-氨基葡萄糖 (GlcNAc-2C12) 引物是通过十二聚糖-1-醇、十三聚糖-7-醇和戊聚糖-13-醇分别与过乙酰氨基葡萄糖进行糖基化合成的。将这些引物引入小鼠 B16 黑色素瘤细胞以制备糖脂。孵育 48 小时后，结果表明 GlcNAc-C12 被拉长，得到 NeuAc-Gal-GlcNAc-C12。GlcNAc-2C6 也被拉长得到 Gal-GlcNAc-2C6 和 NeuAc-Gal-GlcNAc-2C6。另一方面，GlcNAc-2C12 引物没有被延长。显着地，
• Compositions and methods for treatment of inflammatory disorders
  申请人：THE JOHNS HOPKINS UNIVERSITY

  公开号：US10668092B2

  公开（公告）日：2020-06-02

  The present invention relates to methods of treating infectious, inflammatory and post-traumatic disorders by administering various compounds newly discovered to have TLR4 inhibitory activity. In addition to methods of treatment, the present invention further provides for pharmaceutical compositions comprising said compounds, together with a suitable pharmaceutical carrier.

  本发明涉及通过施用新发现的具有 TLR4 抑制活性的各种化合物来治疗感染性、炎症性和创伤后疾病的方法。除治疗方法外，本发明还进一步提供了药物组合物，其中包含上述化合物以及合适的药物载体。
• Glycosylation of dodecyl 2-acetamido-2-deoxy-β-d-glucopyranoside and dodecyl β-d-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-d-glucopyranoside as saccharide primers in cells
  作者：Toshinori Sato、Minako Takashiba、Rumi Hayashi、Xingyu Zhu、Tatsuya Yamagata

  DOI：10.1016/j.carres.2008.01.022

  日期：2008.4

  Syntheses of oligosaccharides expressed on cells are indispensable for the improvement of the functional analyses of the oligosaccharides and their applications. We are developing saccharide primers for synthesizing oligosaccharides using living cells. In this study, dodecyl 2-acetamido-2-deoxy-beta-D-glucopyranoside (GlcNAc-C12) and dodecyl beta-D-galactopyranosyl-(1 -> 4)-2-acetamido-2-deoxy-beta-D-glucopyranoside (LacNAc-C12) were examined for their abilities to prime the syntheses of neolacto-series oligosaccharides in HL60 cells. When GlcNAc-C12 was incubated with HL60 cells in serum-free medium for 2 days, 14 kinds of glycosylated products were collected from the culture medium. They were separated by high-performance liquid chromatography. The sequences of the products were determined to be neolacto-series oligosaccharides including Lewis(X), sialyl Lewis(X), polylactosamine, and sialylpolylactosamine by mass spectrometry. GlcNAc-C12 was also glycosylated by B16 cells and gave sialyllactosamine. Furthermore, LacNAc-C12 gave similar glycosylated products to GlcNAc-C12. (C) 2008 Elsevier Ltd. All rights reserved.
• ANTAGONISTE SPÉCIFIQUE DE TLR4 DANS LE TRAITEMENT DU MYÉLOME MULTIPLE
  申请人：Etablissement Français du Sang

  公开号：EP3558323A1

  公开（公告）日：2019-10-30